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Vacation rentals with a pool in Church-Wellesley

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Church-Wellesley

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Superhost
Condo in Harbourfront
4.88 out of 5 average rating, 141 reviews

Luxury Downtown 2Bed by ScotiaBank Arena + Parking

Welcome to Maple Leafs Square! This stunning 2-bed, 2-bath corner suite offers free parking & breathtaking views of the city, CN Tower & Lake Ontario. Enjoy direct access to essential amenities like a supermarket, liquor store, Starbucks, restaurants, bars & banks. Perfectly located just steps from Union Station, Scotiabank Arena & a short 5-min walk to the CN Tower, Lake & Harbourfront. Convenient access to Billy Bishop Airport & the UP Express from Pearson Airport. Ideal for exploring Toronto!

Top guest favorite
Condo in Fort York
4.98 out of 5 average rating, 210 reviews

Stylish Downtown Toronto Condo with Free Parking

Experience downtown Toronto in a stylish condo! Start your day in a bright kitchen & enjoy coffee on the balcony. Relax with Netflix after exploring the city. Walk to CN Tower, Rogers Centre, Ripley’s Aquarium, Exhibition Place, restaurants & waterfront. Full kitchen, Keurig, 2 desks for work. Building features pool, hot tub, sauna, gym, seasonal rooftop BBQ, free parking & self check-in. Discounts on stays of 7+ nights & non-refundable bookings. Book your unforgettable Toronto getaway today!

Top guest favorite
Home in The Beaches
4.99 out of 5 average rating, 158 reviews

Ask re: FALL Specials-Heated Pool-tub Open 365 Day

Ask about FALL BONUS NIGHTS: BOOK 2 nights-get 3rd for free: Located right by the lake. HEATED private pool and spa. OPEN 365 days- EVEN IN WINTER !! Explore local shops on Queens St. Swim, kayak (provided), volleyball, basketball and tennis courts right beside us. In winter, an outdoor ice rink (skates provided), cross-country ski trails, and lots of walking to be had. We decorate for the holidays, and the house has a real wood burning fireplace. **note quiet hours are 11:00 pm to 7:00AM

Superhost
Condo in Courtice
4.83 out of 5 average rating, 125 reviews

Downtown Toronto 2 BDR Condo CN Tower/Lake Views

Stunning 2 bedroom & 2 bath condo in the heart of downtown Toronto! Breathtaking views of the CN Tower, Lake, and southwest sunset. Steps away from the CN Tower, Scotiabank Arena, Rogers Centre, Union Station (airport express train direct), Convention Centre, Waterfront, and more. FREE PARKING for one vehicle. Luxurious amenities: rooftop pool, indoor pool, hot tubs, sauna, gym, theater room, party rooms. Grocery, Starbucks, restaurants, banks, bars inside the building on the ground floor.

Top guest favorite
Condo in Yorkdale
5 out of 5 average rating, 118 reviews

The Penty: Luxurious Penthouse with Pool, Hot Tub

Welcome to our modern & luxurious corner penthouse! Stylishly designed with lush greenery and upscale touches, this bright space offers comfort, elegance, and a relaxed tropical vibe. Take in stunning panoramic city views and unwind with premium amenities including an outdoor pool, hot tub, and steam room sauna. Just a 15-min drive to downtown. Public transit at the doorstep. 10-min drive to Rogers Stadium. Perfect for discerning guests seeking an elevated stay in Toronto’s vibrant urban core

Top guest favorite
Apartment in Entertainment District
4.97 out of 5 average rating, 39 reviews

CN Tower View 4BD Penthouse+Rogers Centre+Parking

Luxury 4BD 2BR Penthouse w/ CN Tower View | 3 Baths + Free Parking Welcome to your sky-high escape in the heart of downtown Toronto. This stunning 1500sq ft, 2-bedroom, 3-bathroom penthouse at 300 Front Street West offers unbeatable views of the CN Tower and skyline. Perfect for groups, families, or business travelers — comfortably sleeps up to 8 guests. Enjoy a spacious open-concept layout, modern finishes, and a fully equipped kitchen. Free parking included (a rare find in downtown!).

Guest favorite
Loft in Upper Jarvis
4.91 out of 5 average rating, 85 reviews

Modern Downtown Loft with Private Garden

Welcome to this modern and spacious (765 square feet / 71 square meters) one bedroom condo loft in the prestigious Verve Residences and Lofts located minutes away from Yonge & Bloor, Yorkville, the Village, Yonge & Dundas Square, the University of Toronto, two Subway lines and countless other Toronto landmarks, museums and restaurants. This condo loft features luxurious finishes & decor, a king size bed, as well as a rarely found private entrance and garden in the centre of the city.

Top guest favorite
Apartment in Church-Wellesley
5 out of 5 average rating, 18 reviews

Lake Views | Downtown | Charming | by UFT & TMU

Enjoy the best of downtown Toronto in this stylish condo located near Yonge and Wellesley. Perched on a high floor, this unit offers breathtaking views of Lake Ontario and boasts top-tier amenities, including a pool, fully-equipped gym, and a relaxation room, so you can unwind in style. Indulge in renowned spots like Hey Tea and Japadog, right at your doorstep! Enjoy the comfort of living near UofT and TMU, a short 10 minute walk away. Experience downtown living at its finest!

Superhost
Condo in Discovery District
4.91 out of 5 average rating, 32 reviews

Upscale 1 Bed+Den Condo in Downtown Toronto

Experience urban luxury in this stylish 1-bedroom plus den condo in downtown Toronto. Enjoy a modern living area with floor-to-ceiling windows, a fully equipped kitchen, and a comfortable bedroom with a queen-sized bed. The versatile den serves as a workspace or additional sleeping area. Located in a vibrant neighbourhood with easy access to dining, shopping, and entertainment options. Amenities include a pool, gym, jacuzzi and a sauna.

Superhost
Condo in Entertainment District
4.83 out of 5 average rating, 239 reviews

⭐️KING Bed Luxury Condo - CN Tower View + Parking⭐️

Ask about discounts! Welcome to my cozy and modern condo, where you will find yourself in the heart of Toronto - CN Tower, Scotiabank Arena, Rogers Centre, Metro Toronto Convention Centre - all just steps outside your door! Enjoy beautiful views of the city skyline, harbor, and CN Tower. Two bedrooms, two full separate bathrooms, and pullout sofas will comfortably sleep 6, but we can accommodate 8 with extra mattresses.

Guest favorite
Condo in Downtown Toronto
4.95 out of 5 average rating, 19 reviews

Enjoy the City Skyline View with Pool & Gym

- Stay in a luxurious condo centrally located for exploring all of downtown. - Enjoy the comfort of a pillow-top king bed and all-inclusive modern amenities. - Close walking distance to top shops, dining & iconic attractions like the CN Tower. - Relax on the balcony with skyline views, or unwind by the building's pool & sauna. - Reserve now to experience vibrant city life and seamless convenience firsthand!

Superhost
Condo in Mississauga
4.84 out of 5 average rating, 285 reviews

Beautiful Cozy 1 BR Condo👌🔥 Steps to SQ1! 👍

This beautiful sunfilled condo is newly furnished and well cared for, equipped with everything you need to make you feel right at home! Free Wifi included with Netflix access and underground parking. Amenitites in the building include a swimming pool and gym. located very conveniently in the heart of Mississauga, steps to Square one, Hwy 403, Pearson Airport and only a short drive to Downtown Toronto.

Popular amenities for Church-Wellesley rentals with a pool

Quick stats about vacation rentals with a pool in Church-Wellesley

  • Total rentals

    80 properties

  • Nightly prices starting at

    $20 before taxes and fees

  • Total number of reviews

    810 reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

Destinations to explore

  1. Airbnb
  2. Canada
  3. Ontario
  4. Toronto
  5. Church-Wellesley
  6. Rentals with pools